Our invention relates to the novel reaction product which is the schiff base of ethyl vanillin and methyl anthranilate, the compound having the structure: ##STR5## and the organoleptic use thereof in augmenting or enhancing the aroma of perfume compositions, colognes and perfumed articles and in enhancing or augmenting the effect of deodorancy; as a maskant for malodors emanating from the axillary regions of mammalian species.
Inexpensive chemical compositions of matter which can provide sweet, vanilla bean-like and sassafras aroma profiles with sweet topnotes and which are highly substantive and long-lasting are highly desirable in the art of perfumery. Many of the natural materials which provide such fragrances and contribute desired nuances to perfumery compositions as well as perfumed articles including solid or liquid anionic, cationic, nonionic or zwitterionic detergents, fabric softener compositions and fabric softener articles are high in cost, vary in quality from one batch to another and/or are generally subject to the usual variations of natural products.
Still more desirable are materials which can both provide useful fragrance effects including high substantivity and a long-lasting fragrance and also provide a deodorancy effect whereby malodors can be masked by means of the use of the compound in, for example, the axillary regions of mammalian species including human beings.
Reaction products of carbonyl-containing compounds and amine-containing compounds are well known in the art of flavoring and in the art of of perfumery. Thus, U.S. Pat. No. 4,618,501 issued on Oct. 21, 1986 discloses the flavoring of foodstuffs with alpha,beta-keto-amines and states that an alpha,beta-keto-amine having a nutty corn, cereal aroma may be used for flavoring compositions for foods having the structure: ##STR6## wherein R.sub.1, R.sub.2 and R.sub.3 are selected from the group consisting of a saturated or unsaturated alkyl straight or branched chain hydrocarbons having from 1-3 carbon atoms.
U.S. Pat. No. 3,625,710 issued on Dec. 7, 1971 discloses the use of aldimines as chocolate-like flavors which aldimines are resulting from the reaction product of amines and aldehydes, for example, N-isobutylidenefurfurylamine, N-isopentylidenefurfurylamine, N-isopentylideneisopentylamine.
Schiff bases are also well known in the art of perfumery. Thus, for example, Chemical Abstracts Volume 103, 1985, No. 123134z (Abstract of Japan Kokai No. 60/78951 discloses the use in perfumery of compounds having the structure: ##STR7##
Arctander "Perfume and Flavor Chemicals (Aroma Chemicals)", Volume II, published by Author in 1969 discloses the organoleptic properties of the schiff base of methyl anthranilate and vanillin having the structure: ##STR8## thusly: ##STR9##
Arctander also discloses the organoleptic properties of vanillin-ethyl carbonate-phenetidine, thusly: ##STR10##
The compound of our invention having the structure: ##STR11## has unexpected, unobvious and advantageous organoleptic properties including deodorancy properties as opposed to the compounds of the prior art including the compound having the structure: ##STR12##
The book "Flavor & Fragrance Materials-1987" published by Allured Publishing Corporation, P. O. Box 318, Wheaton, Illinois 60189-0318 discloses on page 154 the commercial availability of the following schiff bases:
Methyl anthranilate and amyl cinnamic aldehyde; PA0 Methyl anthranilate and hydroxy citronellal; PA0 Methyl anthranilate and lilial; PA0 Methyl anthranilate and anisic aldehyde; PA0 Methyl anthranilate and decanal; PA0 Methyl anthranilate and lyral; PA0 Methyl anthranilate and iso-nonylaldehyde; PA0 Methyl anthranilate and phenylacetaldehyde.
Schiff bases are also known to be useful as intermediates in producing other fragrance materials. Thus, U.S. Pat. No. 3,898,283 issued on Aug. 5, 1975 discloses novel schiff base intermediates used in producing 4 or 5 phenylpentenals having the structure: ##STR13## wherein X is a moiety selected from the group consisting of: ##STR14## and wherein R.sub.a is hydrogen or methyl.
Nothing in the prior art however discloses the novel reaction products or reaction product mixtures of our invention having unobvious, unexpected and advantageous organoleptic properties.
Indeed, nothing in the prior art is indicative of the novel schiff base reaction products of our invention having deodorizing properties that is, having a deodorant value of 0.50 up to 3.5 as measured by the deodorant value test described in U.S. Pat. No. 4,304,679 incorporated by reference herein or having a Lipoxidase-inhibiting capacity of at least 50% and a Malodour reduction value of from 0.25 up to 3 as measured by the Malodour reduction value test disclosed in U.S. Pat. No. 4,663,068 incorporated by reference herein.